Abstract: Enantioselective organocatalysis, employing small chiral organic molecules to promote different chemical transformations, has received widespread attention over the past decade. Inspired by the powerful capabilities of aminocatalysis, our group has initiated a project to develop new chiral pyrrolidines with a mono-aryl group that would complement the existing diarylprolinol ether and imidazolidinone catalysis. D-Arabinose was conveniently chosen as the starting material because of its built-in chirality and its ready commercial availability in large quantities for both enantiomers. Chiral hydroxylated pyrrolidine catalysts were synthesized from D-arabinose in a straightforward manner. Various aromatic substituents to the amine can be introduced readily by a Grignard reaction, which enables facile optimization of the catalyst performance. Applications of these chiral pyrrolidines to enantioselelctive intramolecular Diels-Alder reactions with and without de-symmetrization will be presented in the seminar.